KR100229561B1 - 리파제와 수용성 4급 암모늄화합물을 함유하는 세제조성물 - Google Patents

리파제와 수용성 4급 암모늄화합물을 함유하는 세제조성물 Download PDF

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KR100229561B1
KR100229561B1 KR1019930702124A KR930702124A KR100229561B1 KR 100229561 B1 KR100229561 B1 KR 100229561B1 KR 1019930702124 A KR1019930702124 A KR 1019930702124A KR 930702124 A KR930702124 A KR 930702124A KR 100229561 B1 KR100229561 B1 KR 100229561B1
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detergent composition
formula
water
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알라스테어존프리티
로빈스코트하그로브
앙드레세자르벡크
알프레트부시
앙드레크리스티안콘벤츠
쟝-폴부띠끄
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데이비드 엠 모이어
더 프록터 앤드 갬블 캄파니
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Abstract

특정한 수용성 4급 암모늄 화합물과 리파제 효소를 함유하는, 오염물 제거 특성/재부착방지 특성이 증진된 세제 조성물이 기술되어 있다.

Description

[발명의 명칭]
리파제와 수용성 4급 암모늄 화합물을 함유하는 세제 조성물
[기술 분야]
본 발명은 오염물 제거 특성, 특히 트리글리세라이드-함유 오염물에 대한 오염물 제거 특성이 향상된 세제 조성물에 관한 것이다.
[발명의 배경]
효소 세제 조성물은 당업계에 널리 공지되어 있다.
특히, 리파제는 다수의 특허 문헌에 세제 조성물에 가능한 효소로서 기술되어 있으며, 이러한 문헌의 대표적인 예로는 세척제용 첨가제 제조에 있어서의 리파제의 용도를 기술하고 있는 미합중국 특허 제4,011,169호 뿐만 아니라 모두 오염물 제거제로서 리파제를 함유하는 특정 세제 조성물에 관한 것인 EP-A- 제205,208호, 제206,390호 또는 제341,999호가 있다.
특정 미생물로부터 리파제를 제조하는 방법은, 예를 들어, EP-A- 제214,761호 및 제258,068호에 기술되어 있다.
한편, 직물 세정 특성 및 연화 특성을 나타내는 세제 조성물 중에서의 특정한 수용성 4급 암모늄 화합물의 용도는 공지되어 있으며, 특히 EP-A-제26,529호는 특정의 수용성 4급 암모늄 화합물의 사용으로 직물 세정 및 연화 특성이 개선된 세제 조성물을 기술하고 있다.
본 발명에 이르러, 리파제 효소와 특정한 수용성 4급 암모늄 화합물의 배합물이 예기치않게도 직물로부터의 트리글리세라이드-함유 오염물의 제거율을 증가시키며, 이러한 배합성분들중 한 성분만을 사용함으로써 이전에 달성할 수 없었던 오염물-재부착 방지 효과를 수득할 수 있음이 밝혀졌다.
[발명의 요약]
본 발명은 리파제 효소를 추가로 함유함을 특징으로 하는, 계면활성제 및 일반식(i) 또는(ii)의 수용성 4급 암모늄 화합물을 포함하는 세제 조성물에 관한 것이다.
상기식에서, R1은 C8-C16알킬이거나 일반식 R5-T--R6의 그룹[여기서, T는 O, NH 또는 N-C1-4알킬이고, R5는 2가 C1-C3알킬렌 그룹 또는 일반식(C2H4O)m의 그룹(여기서, m은 1 내지 8의 수이다)이고, R6은 C12-C14알킬이다]이고, R2,R3및 R4는 각각 독립적으로 C1-C4알킬 또는 하이드록실 알킬, 벤질, 또는 일반식-(C2H4O)xH의 그룹(여기서, x는 2 내지 5이다)이며, 단 R2,R3또는 R4중 하나 이하가 벤질이고, X-는 음이온이며, Q는 CH, CH2또는 N 이고, n은 2, 3 또는 4, 바람직하게는 2이다.
상기한 4급 암모늄 염은 바람직하게는 R1이 C12-C15알킬이고 R2,R3및 R4가 바람직하게는 메틸 및 하이드록시에틸 그룹 중에서 선택된 종으로 부터 선택된다.
본 발명의 조성물은 과립 형태, 압축된 과립 형태 또는 액체 형태로 존재한다.
[발명의 상세한 설명]
수용성 4급 암모늄 화합물
본 발명의 조성물에 유용한 수용성 4급 암모늄 화합물은 일반식(i) 또는 (ii)를 갖는다.
상기식에서, R1은 C8-C16알킬이거나 일반식 R5-T--R6의 그룹[여기서, T는 O, NH 또는 N-C1-4알킬이고, R5는 2가 C1-C3알킬렌 그룹 또는 일반식(C2H4O)m의 그룹(여기서, m은 1 내지 8의 수이다)이고, R6은 C12-C14알킬이다]이고, R2,R3및 R4는 각각 독립적으로 C1-C4알킬 또는 하이드록실 알킬, 벤질, 또는 일반식-(C2H4O)xH의 그룹(여기서, x는 2 내지 5이다)이며, 단 R2,R3또는 R4중 하나 이하가 벤질이고, X-는 음이온이며, Q는 CH, CH2또는 N 이고, n은 2, 3 또는 4, 바람직하게는 2이다.
R1으로서 바람직한 알킬 쇄는 특히, 알킬 그룹이 코코넛 또는 팜핵(palm kernel) 지방으로부터 유도된 쇄의 혼합물이거나 올레핀 형성 또는 옥소 알콜 합성에 의해 합성적으로 유도된, C12-C15알킬이다. R2, R3및 R4로서 바람직한 그룹은 메틸 및 하이드록시에틸 그룹이고 음이온 X는 할라이드, 메토설페이트, 아세테이트 및 포스페이트 이온으로부터 선택될 수 있다.
본원에서 사용하기에 적합한 일반식(i)의 4급 암모늄 화합물의 예로는 코코넛 트리메틸 암모늄 클로라이드 또는 브로마이드, 데실 트리 에틸 암모늄 클로라이드, 데실 디메틸 하이드록시에틸 암모늄 클로라이드 또는 브로마이드, C12-15디메틸 하이드록시에틸 암모늄 클로라이드 또는 브로마이드, 코코넛 디메틸 하이드록시에틸 암모늄 클로라이드 또는 브로마이드, 미리스틸 트리메틸 암모늄 메틸 설페이트, 라우릴 디메틸 벤질 암모늄 클로라이드 또는 브로마이드, 라우릴 디메틸(에텐옥시)4암모늄 클로라이드 또는 브로마이드, 콜린 에스테르 (R1이 CH2-O--C12-14알킬이고, R2, R3및 R4가 메틸인 일반식(i)의 화합물), 및 디알킬 이미다졸린[일반식(i)의 화합물]이 있다.
본 발명의 조성물의 상술한 수용성 양이온성 성분은 pH 10에서 0.1% 수용액 중의 양이온 형태로 존재할 수 있다.
수용성 양이온 화합물은 세제 조성물의 0.1 내지 10중량%의 양으로 존재한다.
[리파제 효소]
본 발명의 조성물은 광범위한 리파제중에서, 특히, 예를 들어, 유럽 특허 제0 214 761호, 제0 258 068호, 제0 205 208호 및 제0 206 390호에 기술되어 있는 리파제 중에서 선택될 수 있는 리파제 효소를 포함한다. 예를 들어, 다음과 같은 상표명으로 시판되고 있는 리파제 제제가 특히 적합하다 : 노보 리폴라제(Novo LipalaseR), 아마노(Amano) 리파제 CE, P, B, AP, M-AP, AML 및 CES, 및 메이토(Meito) 리파제 MY-30, OF 및 PL 뿐만 아니라 에스테라제 MM, 리포짐(Lipozym), SP225, SP285, 사이켄(Saiken) 리파제, 엔제코(Enzeco)리파제, 토요 조조(Toyo Jozo) 리파제 및 디오신트(Diosynth) 리파제.
효소는 적절한 리파제 유전자, 예를 들어, 휴미콜라 라누기노사(Humicola lanuginosa) 또는 이의 돌연변이체로부터의 리파제 유전자를 추출후, 당해 유전자 또는 이의 유도체를 아스퍼질러스(Aspergillus)와 같은 적합한 생산 유기체중에 도입하여 발현시킴으로써 유전 공학적으로 처리 될 수 있다.
WO 제88/02775호(Novo), 유럽 특허 제 0 243 338호(Labofina) 및 유럽 특허 제0 268 452호(Genencor)에 기술되어 있는 기술을 적용하여 채택할 수 있다.
리파제는 본 발명의 조성물 중에 조성물 1g당 10 내지 5,000LU의 양으로 존재한다.
1LU는 하기 조건하에서 1분 이내에 적정 가능한 부티르산 1μmol을 방출하는 지방 분해 활성을 나타낸다 :
온도 : 30℃
pH : 7.0
기질 : 트리부티린
[노보(NOVO) 출판물 AF 95.4/1에 상세히 기술되어 있음].
리파제가 리폴라제R100kLU인 경우, 이의 양은 총 조성물의 0.01 내지 5중량% 범위가 통상적이다.
[계면활성제]
광범위한 계면활성제를 본 발명의 세제 조성물에 사용할 수 있다. 음이온성, 비이온성, 양쪽성 및 쯔비터 이온성 부류 및 이들 계면활성제 종류의 대표적인 목록은 1972년 5월 23일 에 노리스(Norris)에게 특허된 미합중국 특허 제3,664,961호에 기술되어 있다.
본원에서는 음이온성 계면활성제의 혼합물, 특히 중량비가 5:1 내지 1:2, 바람직하게는 3:1 내지 2:3, 보다 바람직하게는 3:1 내지 1:1인 설포네이트와 설페이트 계면활성제의 혼합물이 특히 적합하다. 바람직한 설포네이트에는 알킬 라디칼의 탄소 원자 수가 9 내지 15, 특히 11 내지 13인 알킬 벤젠 설포네이트, 및 지방산이 C12-18지방 공급원, 바람직하게는 C16-18지방공급원으로부터 유도된 알파- 설폰화된 메틸 지방산 에스테르가 포함된다. 각각의 경우에, 양이온은 나트륨 모노 또는 폴리에탄올아민 또는 암모늄으로 부터 선택된 알칼리 금속이다. 바람직한 설페이트 계면활성제는 임의로 알킬 라디칼의 탄소수가 10 내지 20, 바람직하게는 10 내지 16이고 평균 에톡실화도가 1 내지 6인 에톡시 설페이트와의 혼합물로서 존재하는, 알킬 라디칼의 탄소수가 12 내지 18인 알킬 설페이트이다. 본원에서 바람직한 알킬 설페이트의 예로는 수지 알킬 설페이트, 코코넛 알킬 설페이트 및 C14-15알킬설페이트가 있다. 각 경우에 양이온은 또한 알칼리 금속 양이온이다.
본 발명에 유용한 비이온성 계면활성제의 한 부류는 평균 친수성-친지성 균형도(HLB)가 8 내지 17, 바람직하게는 9.5 내지 13.5, 보다 바람직하게는 10 내지 12.5인 계면활성제를 제공하는, 소수성 잔기와 에틸렌 옥사이드의 축합물이다.
소수성(친지성) 잔기는 지방족 또는 방향족 특성을 나타낼 수 있으며, 임의의 특정한 소수성 그룹과 축합 되는 폴리옥시에틸렌 그룹의 길이를 용이하게 조정하여 친수성 원소와 소수성 원소 사이에 목적하는 균형도를 갖는 수용성 화합물을 수득할 수 있다.
당해 유형의 특히 바람직한 비이온성 계면활성제는 알콜 1mol당 에틸렌 옥사이드 3 내지 8mol을 함유하는 C9-C151급알콜 에톡실레이트, 특히 알콜 1mol당 에틸렌 옥사이드 6 내지 8mol을 함유하는 C14-C151급알콜 및 알콜 1mol당 에틸렌 옥사이드 3 내지 5mol 을 함유하는 C12-C141급알콜이다.
비이온성 계면활성제의 다른 부류에는 반응하지 않은 지방 알콜 10%미만 및 단쇄 알킬 폴리글루코사이드 50% 미만을 포함하는, 하기 일반식의 알킬 폴리글루코사이드 화합물이 포함된다.
RO(CnH2nO)tZx
상기식에서, Z는 글루코오즈로부터 유도된 잔기이고, R은 탄소원자 12 내지 18개를 함유하는 소수성 포화 알킬 그룹이며, t는 0 내지 10이고, n은 2 또는 3이며, x는 1.3 내지 4이다.
당해 유형의 화합물 및 세제에서의 이의 용도는 EP-B 제0 070 077호, 제0 075 996 및 제 0 094 118호에 기술되어 있다.
하기 일반식의 폴리하이드록시 지방산 아미드 계면활성제 또는 이의 알콕실화된 유도체도 또한 비이온성 계면활성제로서 적합하다.
상기식에서, R1은 H, C1-4하이드로카빌, 2-하이드록시에틸, 2-하이드록시프로필 또는 이들의 혼합물이고, R2는 C5-31하이드로카빌이며, Z는 쇄에 직접 연결된 3개 이상의 하이드록실을 갖는 선형 하이드로카빌 쇄를 함유하는 폴리하이드록시하이드로카빌이다. 바람직하게는, R1은 메틸이고, R2는 직쇄의 C11-15알킬 또는 알케닐 쇄(예: 코코넛 알킬 또는 이의 혼합물)이고, Z는 환원당( 예: 글루코오즈, 프럭토오즈, 말토오즈, 락토오즈등)으로부터 환원성 아민화 반응을 통해 유도된다.
또 다른 부류의 계면활성제로는 아민 옥사이드와 같은 반극성 계면활성제가 있다.
적합한 아민 옥사이드는 모노 C8-C20, 바람직하게는 C10-C14N- 알킬 또는 알케닐 아민 옥사이드 및 프로필렌-1,3-디아민디옥사이드 중에서 선택되며, 이때 잔류하는 N 위치는 메틸, 하이드록시에틸 또는 하이드록시프로필 그룹에 의해 치환된다.
또 다른 부류의 계면활성제로는 폴리아민계 종과 같은 양쪽성 계면활성제가 있다.
계면활성제의 혼합물 유형, 더욱 특히는 음이온성-비이온성 계면활성제의 혼합물이 바람직하다. 세제 조성물은 계면활성제 1 내지 70중량%를 포함할 수 있으나, 통상적으로 계면활성제는 본원의 조성물중에 1 내지 30중량%, 보다 바람직하게는 10 내지 25중량%의 양으로 존재한다.
바람직하게는, 음이온성 계면활성제에 대한 본원의 수용성 4급 암모늄 화합물의 몰비는 1:1 미만, 바람직하게는 1:1.5 미만이어야 한다. 강력 세탁 제형과 같은 본 발명의 바람직한 양태에서는, 몰비가 1:2 미만이어야 한다.
[임의 성분]
통상적으로, 본 발명의 조성물은 통상적으로 세제 조성물의 일부를 형성하는 임의 성분을 포함한다. 본 발명의 조성물은 대표적으로 세척 증강제를 함유한다.
알루미노실리케이트 물질, 규산염, 폴리카복실레이트 및 지방산, 에틸렌디아민 테트라아세테이트와 같은 물질, 아미노 폴리포스포네이트, 특히 에틸렌디아민 테트라메틸렌 포스폰산 및 디에틸렌 트리아민 펜타 메틸렌포스폰산과 같은 금속 이온 봉쇄제를 포함하는 모든 통상적인 증강제 시스템이 본원에서 사용되기에 적합하다. 환경적 이유에 기인하여 명백히 덜 바람직하긴 하지만, 포스페이트 증강제를 또한 본원에 사용할 수도 있다.
적합한 증강제는 무기 이온 교환 물질, 통상적으로는 수화된 무기 알루미노실리케이트 물질, 보다 특히는 수화된 제올라이트 A, X, B 또는 HS와 같은 수화된 합성 제올라이트일 수 있다.
다른 적합한 무기 증강제 물질은 층상 규산염, 예를 들어, SKS-6(제조회사: Hoechst)이다. SKS-6은 규산나트륨(Na2Si2O5)으로 이루어진 층상 결정성 규산염이다.
본원에서 사용하기에 적합한 폴리카복실레이트에는 일반식RCH(COOH)CH2(COOH)의 석신산 유도체(여기서, R은 C10-20알킬 또는 알케닐, 바람직하게는 C12-16알킬 또는 알케닐이거나 하이드록실, 설포 설폭실 또는 설폰 치환제에 의해 치환될 수 있다)인 시트르산, 바람직하게는 수용성 염형태의 시트르산이 포함된다.
특정 예로는 라우릴 석시네이트, 미리스틸 석시네이트, 팔미틸 석시네이트, 2-도데세닐 석시네이트, 2-테트라데세닐 석시네이트 등이 있다.
석시네이트 증강제는 나트륨, 칼륨, 암모늄 및 알칸올 암모늄 염을 포함하는 이의 수용성 염 형태로 사용하는 것이 바람직하다.
기타의 적합한 폴리카복실레이트로는 미합중국 특허 제4,663,071호에 기술되어 있는 바와 같은 옥소디석시네이트 및 타르트레이트 모노석신산과 타르트레이트 디석신산의 혼합물이 있다.
특히, 본 발명을 액체 상태에서 수행하는 경우, 본원에서 사용하기에 적합한 지방산 증강제는 포화 또는 불포화 C10-18지방산 뿐만 아니라 상응하는 이의 비누이다. 알킬 쇄 중에 12 내지 16개의 탄소 원자를 함유하는 포화 종이 바람직하다.
바람직한 불포화 지방산은 올레산이다.
과립형 조성물에 사용하기에 바람직한 증강제 시스템에는 제올라이트 A와 같은 수불용성 알루미노실리케이트 증강제 및 시트르산과 같은 수용성 카복실레이트 킬레이트제의 혼합물이 포함된다.
본 발명의 조성물에 사용하기 위한 증강제 시스템의 일부를 형성할 수 있는 기타 증강제 물질에는 알칼리 금속 탄산염, 중탄산염, 규산염 등과 같은 무기 물질 및 유기 포스포네이트, 아미노 폴리알킬렌 포스포네이트 및 아미노 폴리카복실레이트와 같은 유기 물질이 포함된다.
기타의 적합한 수용성 유기염으로는 폴리카복실산이 2개 이하의 탄소원자에 의해 서로 분리된 카복실 라디칼 2개 이상을 포함하는 단독-또는 공중합체성 산 또는 이의 염이 있다.
이러한 유형의 중합체는 GB-A-제1,596,756호에 기술되어 있다. 이러한 염의 예로는 분자량이 2,000 내지 5,000인 폴리아크릴레이트 및 분자량이 20,000 내지 70,000, 특히 약 40,000인, 폴리아크릴레이트와 말레산 무수물의 공중합체가 있다.
세척 증강제 염은 통상적으로 조성물의 10 내지 80중량%, 바람직하게는 20 내지 70중량%, 가장 통상적으로는 30 내지 60중량%의 양으로 포함된다.
기타 임의 성분에는 직물 연화제(예 : 스멕타이트 점토), 추가의 중합체(예 : 폴리에틸렌 옥사이드, 폴리비닐피롤리돈, 폴리비닐알콜 등), 표백제, 표백 활성화제, 서드(sud)억제제 뿐만 아니라 프로테아제, 아밀라제, 셀룰라제, 퍼옥시다제, 옥시다제중에서 선택된 기타의 효소가 포함된다.
[조성물의 형태]
본 발명의 조성물은 과립 형태, 특히 압축된 과립 형태로 존재할 수 있고, 즉 당해 조성물은 통상적인 과립형 세제와 비교하여 "무기 충전제 염" 을 보다 적은 양으로 함유하는 본 발명에 따라 통상적인 과립형 세제 조성물 보다 밀도가 비교적 높다. 통상적인 충전제 염은 설페이트 및 클로라아드의 알칼리 토금속 염, 대표적으로는 황산나트륨이고, "압축" 세제는 통상적으로 충전제 염 10% 이하를 포함한다.
또한 본 발명의 조성물은 액체 형태로도 존재할 수 있으며, 유기 용매, 특히 에탄올과 같은 당해 조성물의 대표적 성분을 포함한다.
[실시예]
[실시예1]
다음과 같은 세제 조성물을 제조한다.
상기 조성물들의 오염물 제거율(%)과 백색 유지 효과를 비교 한다.
세탁 전후의 올리브유/ 수단 레드(Sudan red)로 오염된 견본 조각의 반사율 측정치를 비교하여 오염물 제거율(%)을 평가한다. 방법은 다음과 같다 : 올리브유 제거율의 가시도를 증진시키기 위해, 올리브유를 수단 레드(오일 가용성 염료)로 염색한다. 반사율 값을 판독함으로써 오염물 제거율(%)을 측정할 수 있다.
당해 반사율 값(수단 레드 농도)과 올리브유의 실질적 제거율과의 관계를 증명하기 위해, 올리브유로 오염시킨 견본 조각을 세척 전후에 추출한다.
추출물을 두가지 방법으로, 즉 비중계를 이용하는 방법 및 적외선 분광 분석법(1735㎝-1)을 이용하는 방법으로 측정한다. 결과는 다음과 같다 :
백색 유지 효과는 제거된 오염물의 %로서 오염물 재부착률에 상응한다.
이는 다음과 같이 계산한다 :
당해 효과를 모니터링하기 위해, 오염되지 않은 견본 조각의 반사율을 측정한다.
시험 조건은 다음과 같다 :
런드로미터 장치
40℃ 가열 사이클
세제 농도 : 6g/l
수 경도 : 2.5 mmol/l
세척액 : 200ml
세탁물 : 7 x 7㎝(3g)의 폴리에스테르 견본 조각 6개, 이중 4개는 각각 50μl의 올리브유로 오염된 견본 조각이고, 나머지 2개는 오염되지 않은 견본 조각임.
주기 : 2
결과는 다음과 같다.
[결과에 대한 논의]
오염물(트리글리세라이드-함유 오염물) 제거율 및 백색 유지 효과 측면에서의 본 발명에 따른 조성물의 우수성이 확실히 증명된다.
[상승작용 효과]
실시예1의 오염물 제거율(%) 및 백색 유지 효과를 조성물 B 및 C의 결과의 합과 비교한다.
상기 결과는 실시예1의 결과가 보다 더 우수함을 보여주며 상승 작용이 있음을 증명한다(오염물 제거율(%)은 증가하고 재부착된 오염물의 %(WM)는 감소하였다).
또한, 하기 세제 조성물을 제조한다 :

Claims (3)

  1. 설포네이트 음이온성 계면활성제, 설페이트 음이온성 계면활성제 또는 이의 혼합물을 포함하는 음이온성 계면활성제와 알콜 1mol당 에틸렌 옥사이드 3 내지 8mol을 함유하는 C9-C151급 알콜 에톡실레이트를 포함하는 비이온성 계면 활성제의 혼합물을 포함하는 계면활성제 1 내지 70중량%와 일반식(i) 또는 (ii)의 수용성 4급 암모늄 화합물 0.1 내지 10중량%를 수용성 4급 암모늄 화합물에 대한 계면활성제의 몰비가 1:1 이상이도록 포함하며, 조성물 1g당 10 내지 5,000LU을 제공하기에 충분한 리파제 효소 0.36 내지 1.0중량%를 추가로 함유함을 특징으로 하는 세제 조성물.
    상기식에서, R1은 C8-C16알킬 또는 일반식 R5-T--R6의 그룹[여기서, T는 O, NH 또는 N-C1-4알킬이고, R5는 2가 C1-C3알킬렌 그룹 또는 일반식(C2H4O)m의 그룹(여기서, m은 1 내지 8의 수이다)이고, R6은 C12-C14알킬이다]이고, R2,R3및 R4는 각각 독립적으로 C1-C4알킬 또는 하이드록실 알킬, 벤질, 또는 일반식-(C2H4O)xH의 그룹(여기서, x는 2 내지 5이다)이며, 단 R2,R3또는 R4중 하나 이하가 벤질이고, X-는 음이온이며, Q는 CH, CH2또는 N 이고, n은 2, 3 또는 4이다.
  2. 제1항에 있어서, 4급 암모늄 염이 R1이 C12-C15알킬이고 R2,R3및 R4가 메틸 및 하이드록시 에틸 그룹 중에서 선택된 종으로 부터 선택되는 세제 조성물.
  3. 제1항 또는 제2항에 있어서, 과립 형태, 압축된 과립 형태 또는 액체 형태로 존재하는 세제 조성물.
KR1019930702124A 1991-01-16 1992-01-16 리파제와 수용성 4급 암모늄화합물을 함유하는 세제조성물 KR100229561B1 (ko)

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EP91870006.3A EP0495344A1 (en) 1991-01-16 Compact detergent compositions
EP91870006.3 1991-01-16
PCT/US1992/000073 WO1992013054A1 (en) 1991-01-16 1992-01-16 Detergent compositions containing lipase and water-soluble quaternary ammonium compounds

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TW260704B (ko) 1995-10-21
JPH06504311A (ja) 1994-05-19
EP0646165A1 (en) 1995-04-05

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