季铵盐-15

季铵盐-15
	IUPAC名; 1-(3-Chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride; 1-(3-氯代烯丙基)-3,5,7-三氮杂-1-氮𬭩金刚烷氯化物
识别
CAS号	4080-31-3 ; 51229-78-8（顺式）
PubChem	6435993
ChemSpider	23621565
SMILES	C1N2CN3CN1C[N+](C2)(C3)CC=CCl.[Cl-];
InChI	1/C9H16ClN4.ClH/c10-2-1-3-14-7-11-4-12(8-14)6-13(5-11)9-14;/h1-2H,3-9H2;1H/q+1;/p-1;
InChIKey	UKHVLWKBNNSRRR-REWHXWOFAS
性质
化学式	C9H16Cl2N4
摩尔质量	251.16 g·mol−1
危险性
	GHS危险性符号;
H-术语	H228, H302, H315, H317, H361, H411
P-术语	P210, P273, P280
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

季铵盐-15（英语：Quaternium-15）是一种季铵盐，化学式为C₉H₁₆Cl₂N₄，可用作表面活性剂和防腐剂。它可充当抗微生物剂，因为它会缓慢释放甲醛，这是一种具有杀菌特性的防腐剂。

季铵盐-15和甲醛释放剂一直是受到争论的话题。它们在美国和欧洲经常被禁止使用。^[1]^[2]

合成

季铵盐-15可通过用1,3-二氯丙烯处理乌洛托品制备。

应用

分离出的顺式异构物主要用于化妆品，欧盟的最大允许浓度为0.2%。混合产品可用于更广泛的配方，如可乳化金属切削液、乳胶和乳胶漆、液体地板抛光剂和地板蜡，以及胶水和粘合剂。

安全问题

自2017年以来，欧盟已禁止使用季铵盐-15，美国正在考虑这项法案。^[3]^[4]

过敏反应

季铵盐-15是一种过敏原，可引起皮炎。^[5]许多对季铵盐-15过敏的人也对甲醛过敏。在低pH下，由于杜勒平反应的酸水解，预计会释放大量甲醛。可以使用贴布试验检测对季铵盐-15的敏感性。^[6] 它是手部过敏性接触性皮炎的最常见原因（959例中占16.5%）。^[7]在2005–2006年间，它是贴布试验中第四大流行的过敏原 (10.3%)。^[8]

由于季铵盐-15会释放少量甲醛，^[9]为了应对消费者的压力，强生公司宣布计划到2015年逐步停止在化妆品中使用季铵盐-15。^[10]^[11]

参考资料

^ de Groot, Anton C.; White, Ian R.; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan. Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Contact Dermatitis. 2010, 62 (1): 2–17. PMID 20136875. S2CID 39758546. doi:10.1111/j.1600-0536.2009.01615.x.
^ De Groot, Anton; Geier, Johannes; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan. Formaldehyde-releasers: Relationship to formaldehyde contact allergy, Part 2: Metalworking fluids and remainder. Contact Dermatitis. 22 June 2010, 63 (3): 129–139. PMID 20573163. S2CID 28278068. doi:10.1111/j.1600-0536.2010.01715.x.
^ European Commission notifies bans, restrictions on CMRS in cosmetics. [2 December 2019]. （原始内容存档于2021-01-03）.
^ The cosmetics industry has avoided strict regulation for over a century. Now rising health concerns has FDA inquiring. [2 December 2019]. （原始内容存档于2023-01-17）.
^ Cahill J, Nixon R. Allergic contact dermatitis to quaternium 15 in a moisturizing lotion. Australasia J Dermatol. 2005 Nov;46(4):284–5. PMID 16197434
^ New Zealand Dermatological Society. Quaternium-15 contact allergy. DermNet NZ. [2007-05-31]. （原始内容存档于2016-07-25）.
^ E. Warshaw, et al. "Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994–2004". Journal of the American Academy of Dermatology, Volume 57, Issue 2, pp. 301–314
^ Zug, KA; Warshaw, EM; Fowler, JF Jr; Maibach, HI; Belsito, DL; Pratt, MD; Sasseville, D; Storrs, FJ; Taylor, JS; Mathias, CG; Deleo, VA; Rietschel, RL; Marks, J. Patch-test results of the North American Contact Dermatitis Group 2005–2006. Dermatitis. 2009, 20 (3): 149–60. PMID 19470301. S2CID 24088485. doi:10.2310/6620.2009.08097.
^ Formaldehyde. American Cancer Society. [3 March 2016]. （原始内容存档于2016-11-30）.
^ Johnson & Johnson to phase out potentially harmful chemicals by 2015. CBS News. [3 March 2016]. （原始内容存档于2023-03-23）.
^ Thomas, Katie. The 'No More Tears' Shampoo, Now With No Formaldehyde. The New York Times. 17 January 2014 [3 March 2016]. （原始内容存档于2023-03-23）.

外部链接

DermNet（英语：New Zealand Dermatological Society） dermatitis/quaternium-allergy

Record in the Household Products Database of NLM
Occupational Hazards - Quaternium-15 （页面存档备份，存于互联网档案馆）

[formaldehyde-in-cosmetics-1] Groot, Anton C.; White, Ian R.; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan. Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Contact Dermatitis. 2010, 62 (1): 2–17. PMID 20136875. S2CID 39758546. doi:10.1111/j.1600-0536.2009.01615.x.

[2] De Groot, Anton; Geier, Johannes; Flyvholm, Mari-Ann; Lensen, Gerda; Coenraads, Pieter-Jan. Formaldehyde-releasers: Relationship to formaldehyde contact allergy, Part 2: Metalworking fluids and remainder. Contact Dermatitis. 22 June 2010, 63 (3): 129–139. PMID 20573163. S2CID 28278068. doi:10.1111/j.1600-0536.2010.01715.x.

[EU-3] European Commission notifies bans, restrictions on CMRS in cosmetics. [2 December 2019]. （原始内容存档于2021-01-03）.

[NBC-4] The cosmetics industry has avoided strict regulation for over a century. Now rising health concerns has FDA inquiring. [2 December 2019]. （原始内容存档于2023-01-17）.

[CahillJ-5] Cahill J, Nixon R. Allergic contact dermatitis to quaternium 15 in a moisturizing lotion. Australasia J Dermatol. 2005 Nov;46(4):284–5. PMID 16197434

[6] New Zealand Dermatological Society. Quaternium-15 contact allergy. DermNet NZ. [2007-05-31]. （原始内容存档于2016-07-25）.

[7] E. Warshaw, et al. "Contact dermatitis of the hands: Cross-sectional analyses of North American Contact Dermatitis Group Data, 1994–2004". Journal of the American Academy of Dermatology, Volume 57, Issue 2, pp. 301–314

[Zug_KA_2006-8] Zug, KA; Warshaw, EM; Fowler, JF Jr; Maibach, HI; Belsito, DL; Pratt, MD; Sasseville, D; Storrs, FJ; Taylor, JS; Mathias, CG; Deleo, VA; Rietschel, RL; Marks, J. Patch-test results of the North American Contact Dermatitis Group 2005–2006. Dermatitis. 2009, 20 (3): 149–60. PMID 19470301. S2CID 24088485. doi:10.2310/6620.2009.08097.

[9] Formaldehyde. American Cancer Society. [3 March 2016]. （原始内容存档于2016-11-30）.

[10] Johnson & Johnson to phase out potentially harmful chemicals by 2015. CBS News. [3 March 2016]. （原始内容存档于2023-03-23）.

[11] Thomas, Katie. The 'No More Tears' Shampoo, Now With No Formaldehyde. The New York Times. 17 January 2014 [3 March 2016]. （原始内容存档于2023-03-23）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]